[2.2]Paracyclophane as a bridging unit in the design of organic dyes for sensitized solar cells

Chang, Yuan Jay; Watanabe, Motonori; Chou, Po Ting; Chow, Tahsin J.

doi:10.1039/c1cc16248a

Cited by 32 publications

(17 citation statements)

References 40 publications

(2 reference statements)

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“…[2,2]-Paracyclophane and its reactivity are of great interest to the synthetic chemist as paracyclophanes and their derivatives are widely used reagents in synthetic chemistry (de Meijere & Kö nig, 1997;Elacqua & MacGillivray, 2010;Paradies, 2011;Chang et al, 2012;Elacqua et al, 2012;Vö gtle, 1990;Hopf & Gleiter, 2004;Hopf, 2012;Li et al, 2014;Meyer-Eppler et al, 2014). To obtain the most information on the structure/reactivity relationship a charge density investigation is unequivocally the most informative course of action (Stalke, 2011(Stalke, , 2012aGatti & Macchi, 2012).…”

Section: Introductionmentioning

confidence: 99%

Charge density investigations on [2,2]-paracyclophane – in data we trust

Wolf

Jørgensen

Chen

et al. 2015

Acta Crystallogr Sect B

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Four datasets on [2,2]-paracyclophane were collected in-house and at the Advanced Photon Source at two different temperatures for charge density investigation. Global data quality indicators such as high resolution, high I/σ(I) values, low merging R values and high multiplicity were matched for all four datasets. The structural parameters did not show significant differences, but the synchrotron data depicted deficiencies in the topological analysis. In retrospect these deficiencies could be assigned to the low quality of the innermost data, which could have been identified by e.g. merging R values for only these reflections. In the multipole refinement these deficiencies could be monitored using DRK-plot and residual density analysis. In this particular example the differences in the topological parameters were relatively small but significant.

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Section: Introductionmentioning

confidence: 99%

Charge density investigations on [2,2]-paracyclophane – in data we trust

Wolf

Jørgensen

Chen

et al. 2015

Acta Crystallogr Sect B

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“…The criteria for this purpose were determined on the basis of extensive investigations; these criteria specify rigorous dye design [ 3 , 4 ] in addition to control parameters, such as solvent choice and temperature [ 5 , 6 , 7 , 8 , 9 ]. Consequently, this phenomenon can be applied to dye-sensitized solar cells [ 10 , 11 , 12 ], OLEDs [ 13 , 14 ], and chemosensors [ 15 , 16 , 17 ].…”

Section: Introductionmentioning

confidence: 99%

Selective Formation of Twisted Intramolecular Charge Transfer and Excimer Emissions on 2,7-bis(4-Diethylaminophenyl)-fluorenone by Choice of Solvent

2012

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We designed and synthesized a donor-acceptor-donor dye consisting of a 2,7-disubstituted fluorenone with diethylaminophenyl moieties present as strong electron donating groups. Switching between twisted intramolecular charge transfer (TICT) emission and excimer emission was achieved, with no ground state changes, by simply changing the solvent used. In a nonpolar solvent, excimer emission was observed; with increasing polarity, the emission gradually disappeared, and the TICT emission appeared.

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“…[2.2]Paracyclophane is a widely used scaffold that has been exploited in the development of sensors,12 asymmetric catalysts,13 organic light‐emitting diodes,14 and solar cells 14. For the first time, we exploited this novel scaffold to demonstrate the phane effect on the photochromic phenomenon 11.…”

Section: Introductionmentioning

confidence: 99%

Photochromism of Acetyl‐Cyclophanochromene: Intriguing Stabilization of Photogenerated Colored o‐Quinonoid Intermediates

2015

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The photochromism of a chromene annulated on [2.2]paracyclophane, Ac‐CPC, was investigated. Whereas the parent chromene 2,2‐diphenylbenzopyran shows photoinduced coloration only at very low temperatures, acetyl‐cyclophanochromene Ac‐CPC was found to exhibit room‐temperature photochromism. With no extended conjugation due to absence of any substituents in two cofacially‐oriented aryl rings, the through‐space delocalization of π‐electrons, i.e., the phane effect, manifests nicely leading to the stabilization of the photogenerated colored o‐quinonoid intermediates. The interaction between cofacial aryl rings is supported by the distance between them, as revealed by X‐ray crystal structure analysis. Additionally, electrophile···nucleophile interactions are surmised to be important for intriguingly longer persistence of the photogenerated intermediates of Ac‐CPC relative to the lifetime of the photogenerated intermediate generated from the parent cyclophanochromene, which is devoid of an electron‐withdrawing acetyl group.

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[2.2]Paracyclophane as a bridging unit in the design of organic dyes for sensitized solar cells

Abstract: Organic dyes consisting of a [2.2]paracyclophane unit along the main chromophore are examined for their application in sensitized solar cells. These materials exhibit considerably high values of open-circuit voltage (V(oc)) ranging 0.69-0.72 V, and an overall efficiency up to 3.8%.

Cited by 32 publications

References 40 publications

Charge density investigations on [2,2]-paracyclophane – in data we trust

Charge density investigations on [2,2]-paracyclophane – in data we trust

Selective Formation of Twisted Intramolecular Charge Transfer and Excimer Emissions on 2,7-bis(4-Diethylaminophenyl)-fluorenone by Choice of Solvent

Photochromism of Acetyl‐Cyclophanochromene: Intriguing Stabilization of Photogenerated Colored o‐Quinonoid Intermediates

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